Does a 241-year prison sentence for robbery qualify as cruel and unusual punishment? In Missouri, debate is raging over a decades-old sentencing that some are calling excessive and unfair.

At the center of it all is Bobby Bostic, a man who’s been in prison since 1995. In December of that year, Bostic, then 16 years old, and 18-year-old Donald Hutson robbed a group of volunteers who were delivering Christmas presents. During the incident, they fired a gun at two of the victims, grazing one of them. They then carjacked a woman, with Hutson robbing and fondling her before releasing her; the victim reportedly testified that she believed that Hutson was going to rape her before Bostic, who was driving the car, intervened. The two then threw their guns into the river and used the stolen money to buy marijuana before they were eventually caught.

While Hutson accepted a plea deal and was sentenced to 30 years in prison, Bostic went to trial and was ultimately dealt a much tougher sentence: 241 years in prison for the eight counts of armed criminal action, three counts of robbery, three counts of attempted robbery, two counts of assault, one count of kidnapping, and one count of possession of marijuana he was found guilty of.

More than 20 years later, Bostic, at the age of 39, is still in prison and, with the help of the ACLU, is fighting to have his original sentence appealed.

Evelyn Baker, the judge who sentenced Bostic, is one of over 100 current and former judges, prosecutors, and law enforcement officers who are calling on the Supreme Court to throw out the sentence, WTHR reports. Baker used a firm hand during the initial sentencing, even telling Bostic, who she felt failed to show sufficient remorse, that he would “die in the Department of Corrections.” Now, the retired judge feels that the sentence was too harsh and was partially based on insufficient knowledge of the teenage brain.

As she explained in an op-ed for The Washington Post last month, "Scientists have discovered so much about brain development in the more than 20 years since I sentenced Bostic. What I learned too late is that young people's brains are not static; they are in the process of maturing."

“I thought I was faulting Bostic for his crimes. Looking back, I see that I was punishing him both for what he did and for his immaturity,” she also wrote.

Baker is not alone in joining the fight to free Bostic; among his supporters, Bostic can count former acting U.S. Attorney General Sally Yates and former Whitewater independent counsel Kenneth Starr, the New York Daily News reports.

Unfortunately for Bostic, despite the chorus of support surrounding his appeal, Missouri is defending the original sentence. State Attorney General Josh Hawley recently argued in a U.S. Supreme Court filing that Bostic’s sentence does not violate the Constitution's ban on cruel and unusual punishment; as Hawley pointed out, the 2010 Supreme Court's ruling outlawing life sentences for minors who didn't kill anyone applies only to a sentence for one crime. Bostic was sentenced for 18.

In accordance with his original sentence, Bostic won’t be eligible for parole until he’s 112 years old. At this time, it is reportedly unclear when the justices will decide whether to hear his case.